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Sasha Bonilova was born in Lytsk, Ukraine on May 20, 1987. Growing up, she spent her days picking apples and cherries in her front yard, as well as playing with Transformers toys. She was more or less a self proclaimed tomboy. She also spent a lot of her time learning guitar, as well as studying dance.

At age 17, her family moved to Wisconsin. Once she was 18, she had fully blossomed into the woman she is today, and decided that since this was the land of opportunity, she set off to pursue her dream of becoming a Playboy Playmate. She would eventually move to Chicago, Illinois to attend Harrington College of Design, with the hopes of attaining a degree in interior design. Much to her chagrin, however, Playboy was not holding any open auditions there, so she took her quest to Denver, Colorado. It was there that she was signed by the magazine, eventually leading to her "Miss May" status in 2011, and securing her a spot among the elite Playboy Playmates.

Although Sasha had to travel to Colorado to be chosen as a Playboy model, she continued her schooling in Chicago. Also, having been from out of the country and a very eager learner, she not only speaks Ukrainian and English, but also fluent Russian, with a basic understanding of Polish and German as well. In her free time, she still takes a shine to tomboy activities such as bike riding, and even owns a Yamaha sports bike, painted yellow and blue like the colors of her native Ukraine's flag.